Born Dec. 6, 1929, in Holmes County in the Panhandle, Douglass was among the last of a breed of Florida public servants who guided the state from its rural roots to the diverse mega-state it is today.

He served as chairman of the Florida Constitution Revision Commission in 1997 and 1998, working to update and reshape the state’s constitution. As general counsel to Chiles, he was instrumental in putting together the legal team that led to the landmark legal settlement against Big Tobacco. During the 2000 election-year recount in Florida, Douglass served as lead counsel to former Vice President Al Gore.

His last big job: redrafting a proposed state constitutional amendment that would legalize medical marijuana.

“Whether he was drafting an enlightened constitution or representing someone’s yard man for free because he needed help, Dexter worked always to make life better for regular folks,” said John Newton who served with Douglass on the legal team. “His brilliance and strategic insight quickly converted the entire Gore recount legal team into admirers.”

Douglass, who traces his Florida roots to the early 1800s, never forgot his family’s struggles growing up during the Great Depression. He prided himself on finding a way represent clients even if they couldn’t pay.

“A secretary might come in and say, ‘Isaac’s here with a tub of turnips for you,’ ” he told the St. Petersburg Times in a 1996 profile. “People from New York don’t understand that. Turnips is all he’s got.”

Douglass met Chiles at the University of Florida in 1953, where they both attended law school after serving in the Korean War, each imbued with a sense of daring and invincibility that shaped their careers. They remained lifelong friends, with Douglass serving as the governor’s general counsel and remaining as one of his closest advisers throughout his eight years in office.

Douglass built a legal career arguing before federal and state courts on a range of issues, from the First Amendment to school vouchers to civil rights cases. He was named one of the Best Lawyers in America in three categories and, in 2006, received the Florida Bar Foundation Medal of Honor for “a career spent providing legal services to the powerless.”

Author Jeffrey Toobin, who detailed Florida’s recount saga in his book Too Close to Call, called Douglass “Florida’s James Madison.”

But Douglass was also the kind of lawyer politicians hired to get keep themselves out of jail.

He represented a Supreme Court justice facing impeachment, a comptroller charged with income-tax evasion, a state legislator accused of sexually harassing a staff member, a state senator charged with soliciting bond business from a state agency, several state legislators charged with taking illegal gifts and trips during the 1980s, and the University of Florida basketball coach who was forced out of his job amid NCAA investigations.

In his early days, Douglass was known to celebrate his courtroom victories with a cigar, scotch and cognac. But he told the St. Petersburg Times that that practice ended one night in 1974 when he crashed into “a drunk tree” on a trip to buy cigars. A sympathetic sheriff’s deputy asked whether he had been drinking.

“I said, ‘Why in the hell do you think I hit that tree?’ ” Douglass recalled. The deputy drove him home without giving him a ticket.

“I never joined the AA. I joined the ‘Douglass Association,’ ” he said. “My wife said she’d consider kicking me out if I didn’t quit drinking.”

Next to law and politics, Douglass’ passion was his cattle. He built a 300-acre farm eight miles north of Tallahassee, Anhinga Farm, where he raised and bred prize polled Herefords.

“He was always trying to build a better type of Hereford,” said longtime friend William Jablon, headmaster at Maclay School, a private college prep school near Tallahassee.

“Dexter was one of the brightest people I ever knew,” said Lucy Morgan, former Tampa Bay Times Tallahassee bureau chief. “Sometimes he didn’t like what we wrote about him or his governor, and he would let us know. Several times he and I had shouting matches over the phone, but the next time I’d see him it was as though we had never argued.”

Douglass also served on numerous boards during his career, including the University of Florida Foundation, University of Florida Law Center Board of Trustees and Maclay School.

Appointed by four Florida governors to the Board of the Florida School for the Deaf and the Blind, Douglass served for 16 years as both a member and as chairman. He was appointed by President Lyndon Johnson to the Advisory Board for the National Technical Institute for the Deaf.

Douglass “never prepared an obituary,” Jablon added. “He never thought he was going to die.”

He is survived by his wife, Therese, three daughters and several grandchildren. He was preceded in death by his son, William.